D-chiro-Inositol

D-chiro-Inositol is a stereoisomer of inositol that exhibits activities such as improving glucose metabolism, anti-tumor effects, anti-inflammatory properties, and antioxidant activity. D-chiro-Inositol effectively alleviates cholestasis by enhancing bile acid secretion and reducing oxidative stress. D-chiro-Inositol improves insulin resistance, lowers hyperglycemia and circulating insulin levels, reduces serum androgen levels, and ameliorates some metabolic abnormalities associated with X syndrome by mimicking the action of insulin. Additionally, D-chiro-Inositol can induce a reduction in pro-inflammatory factors (such as Nf-κB) and cytokines (such as TNF-α), thereby exerting anti-inflammatory effects. D-chiro-Inositol may be used in the study of liver cirrhosis, breast cancer, type 2 diabetes, and polycystic ovary syndrome[1][2][3][4][5][6][7][8][9].

Product Specifications

CAS Number

[643-12-9]

UNSPSC

12352211

Hazard Statement

H302, H315, H319, H335

Target

Endogenous Metabolite; FOXO; Microtubule/Tubulin; NF-κB; TNF Receptor

Type

Natural Products

Related Pathways

Apoptosis; Cell Cycle/DNA Damage; Cytoskeleton; Metabolic Enzyme/Protease; NF-κB

Applications

Neuroscience-Neuromodulation

Field of Research

Metabolic Disease

Assay Protocol

https://www.medchemexpress.com/d-chiro-inositol.html

Purity

98.0

Solubility

H2O : 75 mg/mL (ultrasonic)

Smiles

O[C@H]1[C@@H]([C@@H]([C@H]([C@@H]([C@H]1O)O)O)O)O

Molecular Formula

C6H12O6

Molecular Weight

180.16

Precautions

H302, H315, H319, H335

References & Citations

[1]Ostlund RE Jr, et al. A stereospecific myo-inositol/D-chiro-inositol transporter in HepG2 liver cells. Identification with D-chiro-[3-3H]inositol. J Biol Chem. 1996 Apr 26;271 (17) :10073-8.|[2]Zhao SS, et al. D-chiro-inositol effectively attenuates cholestasis in bile duct ligated rats by improving bile acidsecretion and attenuating oxidative stress. Acta Pharmacol Sin. 2018 Feb;39 (2) :213-221.|[3]Cheng F, et al. chiro-Inositol Ameliorates High Fat Diet-Induced Hepatic Steatosis and Insulin Resistance viaPKCε-PI3K/AKT Pathway. J Agric Food Chem. 2019 May 29;67 (21) :5957-5967.|[4]Kim Y, et al. Inhibitory effect of D-chiro-inositol on both growth and recurrence of breast tumor from MDA-MB-231 cancer cells[J]. Natural Product Sciences, 2017, 23 (1) : 35-39.|[5]Gambioli R, et al. New insights into the activities of D-chiro-inositol: a narrative review[J]. Biomedicines, 2021, 9 (10) : 1378.|[6]Iuorno M J, et al. Effects of d-chiro-inositol in lean women with the polycystic ovary syndrome[J]. Endocrine Practice, 2002, 8 (6) : 417-423.|[7]Pintaudi B, et al. The effectiveness of Myo‐inositol and D‐chiro inositol treatment in type 2 diabetes[J]. International journal of endocrinology, 2016, 2016 (1) : 9132052.|[8]Larner J, et al. D‐chiro‐inositol–its functional role in insulin action and its deficit in insulin resistance[J]. Journal of Diabetes Research, 2002, 3 (1) : 47-60.|[9]Fortis-Barrera Á, et al. C ucurbita ficifolia Bouché (Cucurbitaceae) and D-chiro-inositol modulate the redox state and inflammation in 3T3-L1 adipocytes[J]. Journal of Pharmacy and Pharmacology, 2013, 65 (10) : 1563-1576.